Trail Running calendar near Highfield-Cascade 2025-2026

The Barrel Oak 6k is a scenic and challenging cross-country race held at Barrel Oak Winery in Delaplane, Virginia. The course features two laps of a 3k route that winds through vineyards, including gravel dirt roads and some hills, offering varied terrain and elevation. Walkers and leashed pets are..

The C&O Canal 100 is a 100-mile ultramarathon held in Knoxville, Maryland, along the scenic C&O Canal towpath near the Potomac River and Appalachian Mountains. The course features one approximately 40-mile loop followed by two 30-mile loops, starting and finishing at Camp Manidokan. Runners enjoy a..

Farm Park Challenge is a trail running event at Agricultural History Farm Park in Montgomery County, Maryland, presented by My Muddy Shoes. The race offers multi-hour lap formats: 3-Hour, 6-Hour, and 10-Hour challenges, totaling 3, 6, or 10 laps, each start at the top of the hour and must be complet..

The Massanutten Mountain Trails 100 Mile Run will take place in Fort Valley on Saturday 16 May 2026. You can run 100 miles.

The More Miles Last One Standing Challenge is an endurance running event held in Knoxville, Maryland, featuring a unique "last one standing" format. Participants run a 4.167-mile loop, known as "the yard," every hour on the hour, continuing as long as they can complete the distance within the hour...

The Old Dominion 100 Endurance Run, held in Fort Valley, Virginia, is a challenging 100-mile race featuring a diverse course that includes pavement, gravel roads, single-track trails, ATV trails, logging roads, rocks, streams, and mud. This unique event tests runners' versatility across multiple ter..

Ironstone 100K is a 100-kilometer (62-mile) point-to-point ultramarathon in the Alleghenies of central Pennsylvania, spanning Blair, Huntingdon, and Centre counties. The race begins at Canoe Creek State Park and winds through rugged, technical terrain after a fast start along the Lower Trail. There..